Discovery of aminopyridines substituted with benzoxazole as orally active c-Met kinase inhibitors
A series of aminopyridines substituted with benzoxazole were designed and synthesized as very potent c-Met kinase inhibitors. We report the synthesis and biological evaluation of aminopyridines substituted with benzoxazole. The SAR of the aminopyridines was explored to improve the inhibitory activit...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 20; no. 14; pp. 4223 - 4227 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Amsterdam
Elsevier Ltd
15.07.2010
Elsevier |
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| Abstract | A series of aminopyridines substituted with benzoxazole were designed and synthesized as very potent c-Met kinase inhibitors.
We report the synthesis and biological evaluation of aminopyridines substituted with benzoxazole. The SAR of the aminopyridines was explored to improve the inhibitory activity against c-Met and to decrease hERG affinity. These studies led to the discovery of amide 24 which showed good c-Met inhibitory potency, low affinity to hERG and favorable pharmacokinetic properties in rats. |
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| AbstractList | A series of aminopyridines substituted with benzoxazole were designed and synthesized as very potent c-Met kinase inhibitors.
We report the synthesis and biological evaluation of aminopyridines substituted with benzoxazole. The SAR of the aminopyridines was explored to improve the inhibitory activity against c-Met and to decrease hERG affinity. These studies led to the discovery of amide 24 which showed good c-Met inhibitory potency, low affinity to hERG and favorable pharmacokinetic properties in rats. We report the synthesis and biological evaluation of aminopyridines substituted with benzoxazole. The SAR of the aminopyridines was explored to improve the inhibitory activity against c-Met and to decrease hERG affinity. These studies led to the discovery of amide 24 which showed good c-Met inhibitory potency, low affinity to hERG and favorable pharmacokinetic properties in rats. |
| Author | Jung, Heejung Koh, Jong Sung Ryu, Jae Wook Lee, Chong Ock Kang, Nam Sook Cho, Sung Yun Ha, Jae Du Han, Sun-Young Kim, Hyoung Rae Lee, Jongkook |
| Author_xml | – sequence: 1 givenname: Sung Yun surname: Cho fullname: Cho, Sung Yun – sequence: 2 givenname: Sun-Young surname: Han fullname: Han, Sun-Young – sequence: 3 givenname: Jae Du surname: Ha fullname: Ha, Jae Du – sequence: 4 givenname: Jae Wook surname: Ryu fullname: Ryu, Jae Wook – sequence: 5 givenname: Chong Ock surname: Lee fullname: Lee, Chong Ock – sequence: 6 givenname: Heejung surname: Jung fullname: Jung, Heejung – sequence: 7 givenname: Nam Sook surname: Kang fullname: Kang, Nam Sook – sequence: 8 givenname: Hyoung Rae surname: Kim fullname: Kim, Hyoung Rae – sequence: 9 givenname: Jong Sung surname: Koh fullname: Koh, Jong Sung – sequence: 10 givenname: Jongkook surname: Lee fullname: Lee, Jongkook email: jongkook@krict.re.kr |
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| Cites_doi | 10.1126/science.1141478 10.1111/j.1747-0285.2009.00895.x 10.2174/156802608785700061 10.1002/jhet.5570270241 10.4103/1477-3163.44372 10.1016/j.tetlet.2005.03.190 10.1016/j.critrevonc.2004.09.004 10.1158/0008-5472.CAN-06-4443 10.1021/jo0402226 10.1073/pnas.1734128100 10.1016/S1093-3263(02)00164-X 10.1016/j.bmcl.2009.12.109 10.2174/156802608785700016 10.1038/nrd2530 10.2174/156802608785700034 10.1002/cmdc.200800262 10.1021/jm060379l 10.1016/j.canlet.2004.09.044 |
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| Keywords | hERG Aminopyridine Benzoxazole c-Met inhibitor Antineoplastic agent Five membered ring Intravenous administration Rat Nitrogen heterocycle Toxicity Ionic channel Modeling Pyridine derivatives Signal transduction Structure activity relation Six membered ring Piperidine derivatives Molecular model Bicyclic compound Receptor protein-tyrosine kinase Aromatic compound Oxygen nitrogen heterocycle Benzoxazole derivatives Enzyme Hepatocyte growth factor Transferases Rodentia Oral administration Enzyme inhibitor Inhibitor enzyme complex In vitro In vivo Vertebrata Growth factor receptor Mammalia Animal Inhibitor Circulatory system Pharmacokinetics |
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| Snippet | A series of aminopyridines substituted with benzoxazole were designed and synthesized as very potent c-Met kinase inhibitors.
We report the synthesis and... We report the synthesis and biological evaluation of aminopyridines substituted with benzoxazole. The SAR of the aminopyridines was explored to improve the... |
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| SubjectTerms | Administration, Oral Aminopyridine Aminopyridines - administration & dosage Aminopyridines - chemistry Aminopyridines - pharmacokinetics Aminopyridines - pharmacology Animals Antineoplastic agents Benzoxazole Benzoxazoles - chemistry Biological and medical sciences c-Met inhibitor Drug Discovery General aspects hERG Medical sciences Models, Molecular Pharmacology. Drug treatments Protein Kinase Inhibitors - administration & dosage Protein Kinase Inhibitors - chemistry Protein Kinase Inhibitors - pharmacology Rats Receptor Protein-Tyrosine Kinases - antagonists & inhibitors Structure-Activity Relationship |
| Title | Discovery of aminopyridines substituted with benzoxazole as orally active c-Met kinase inhibitors |
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